EP0069641A1 - Polyazetylen leitfähiges Material mit grosser Stabilität und Verfahren zur Herstellung - Google Patents
Polyazetylen leitfähiges Material mit grosser Stabilität und Verfahren zur Herstellung Download PDFInfo
- Publication number
- EP0069641A1 EP0069641A1 EP82401182A EP82401182A EP0069641A1 EP 0069641 A1 EP0069641 A1 EP 0069641A1 EP 82401182 A EP82401182 A EP 82401182A EP 82401182 A EP82401182 A EP 82401182A EP 0069641 A1 EP0069641 A1 EP 0069641A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- dopant
- film
- family
- doping
- polyacetylene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 229920001197 polyacetylene Polymers 0.000 title claims abstract description 13
- 239000004020 conductor Substances 0.000 title claims abstract description 4
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 2
- 239000002019 doping agent Substances 0.000 claims abstract description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052747 lanthanoid Inorganic materials 0.000 claims abstract description 5
- 150000002602 lanthanoids Chemical class 0.000 claims abstract description 5
- 239000010936 titanium Substances 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052693 Europium Inorganic materials 0.000 claims abstract description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims abstract description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052769 Ytterbium Inorganic materials 0.000 claims abstract description 3
- 229910052804 chromium Inorganic materials 0.000 claims abstract description 3
- 239000011651 chromium Substances 0.000 claims abstract description 3
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052742 iron Inorganic materials 0.000 claims abstract description 3
- 229910052750 molybdenum Inorganic materials 0.000 claims abstract description 3
- 239000011733 molybdenum Substances 0.000 claims abstract description 3
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 3
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 3
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052721 tungsten Inorganic materials 0.000 claims abstract description 3
- 239000010937 tungsten Substances 0.000 claims abstract description 3
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000000463 material Substances 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 5
- 238000005086 pumping Methods 0.000 claims description 4
- 229910052723 transition metal Inorganic materials 0.000 claims description 4
- 150000003624 transition metals Chemical class 0.000 claims description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 230000005484 gravity Effects 0.000 claims description 2
- 229910052753 mercury Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000003505 polymerization initiator Substances 0.000 claims description 2
- 238000004891 communication Methods 0.000 claims 1
- 239000004065 semiconductor Substances 0.000 abstract description 3
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- 230000007704 transition Effects 0.000 abstract 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/124—Intrinsically conductive polymers
- H01B1/125—Intrinsically conductive polymers comprising aliphatic main chains, e.g. polyactylenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L49/00—Compositions of homopolymers or copolymers of compounds having one or more carbon-to-carbon triple bonds; Compositions of derivatives of such polymers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
- H10K85/143—Polyacetylene; Derivatives thereof
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Definitions
- the invention relates to polyacetylene made conductive by incorporation of dopant, and in particular in the form of flexible and mechanically resistant film (film).
- the invention encompasses the manufacturing and doping process.
- the European patent application published under No. 0 026 234 on October 16, 1980 gives a process for manufacturing a material whose structure, having microcrystalline fibers, lends itself well to the manufacture of such films.
- This material comprises polyacetylene with a high degree of polymerization and at least one electron accepting dopant such as nitric or sulfuric acid or a mixture of strong acids, or the oxide S 0 3 , a chloride or a boron bromide. , or finally a naphthoquinone optionally substituted using hydrogen, or halogen or a cyano, nitro, alkyl or alkoxy radical.
- a conductivity material can thus be obtained which can vary from 10 -9 ohm .cm to 10 ohm .cm, which, in the form of a film, has acceptable characteristics of flexibility, mechanical strength.
- the conductivity thus obtained is not uniform in the thickness of the material and, moreover, rapidly disappears over time.
- the invention tends to eliminate these drawbacks by replacing conventional dopants with dopants based on heavy elements which have low diffusion coefficients.
- the material according to the invention is composed of polyacetylene and of a dopant constituted by a salt of an element belonging either to the family of transition metals or to the family of lanthanides.
- the transition metals are chromium, nickel, iron, titanium, tungsten and molybdenum used in the form of chloride, and the lanthanides are europium and ytterbium.
- FIG. 1 represents the doping rate as a function of the time of doping proper in two embodiments of the invention
- FIG. 2 represents the conductivities obtained as a function of the amount of dopant in the same embodiments
- FIG. 3 gives comparative characteristics of stability over time, in the case of the invention and in that of a conventional dopant.
- Curves 1 and 2 represent the variations in this rate, respectively in the case of the dopant W C1 6 and the dopant Mo Cl 5 . We see that several days (10 5 to 10 6 seconds) are necessary to bring the dopant level above 0.05.
- the decrease is small and the stabilization takes place at a rate of the order of 0.8.
- the material according to the invention can be used, depending on its conductivity, either as an organic conductor or as a p-type semiconductor, either alone or in combination with an n-type semiconductor. It is applicable to the production of photodiodes and solar cells.
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR8113157 | 1981-07-03 | ||
FR8113157A FR2508914B1 (fr) | 1981-07-03 | 1981-07-03 | Materiau polyacetylene conducteur a grande stabilite et son procede de fabrication |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0069641A1 true EP0069641A1 (de) | 1983-01-12 |
EP0069641B1 EP0069641B1 (de) | 1985-11-13 |
Family
ID=9260191
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP82401182A Expired EP0069641B1 (de) | 1981-07-03 | 1982-06-25 | Polyazetylen leitfähiges Material mit grosser Stabilität und Verfahren zur Herstellung |
Country Status (5)
Country | Link |
---|---|
US (1) | US4481132A (de) |
EP (1) | EP0069641B1 (de) |
JP (1) | JPS588747A (de) |
DE (1) | DE3267397D1 (de) |
FR (1) | FR2508914B1 (de) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS61254669A (ja) * | 1985-05-07 | 1986-11-12 | Katsumi Yoshino | 磁性導電性高分子 |
US4927897A (en) * | 1987-07-02 | 1990-05-22 | Fuji Photo Film Co., Ltd. | Metal-containing organic polymer and use thereof |
JPH0731171Y2 (ja) * | 1988-04-05 | 1995-07-19 | 東洋濾紙株式会社 | 被検液検査体 |
FR2678762B1 (fr) * | 1991-07-02 | 1993-09-17 | Thomson Csf | Materiaux conducteurs a base de polymere conducteur encapsule. |
KR101367585B1 (ko) * | 2006-02-28 | 2014-02-25 | 꼼미사리아 아 레네르지 아토미끄 에뜨 옥스 에너지스 앨터네이티브즈 | p-도핑된 유기 반도체를 포함하는 전자 부품 |
US7847364B2 (en) * | 2007-07-02 | 2010-12-07 | Alcatel-Lucent Usa Inc. | Flexible photo-detectors |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4204216A (en) * | 1978-05-04 | 1980-05-20 | University Patents, Inc. | Electrically conducting doped polyacetylene film exhibiting n-type electrical conductivity and method of preparing same |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4222903A (en) * | 1978-05-04 | 1980-09-16 | University Patents, Inc. | P-Type electrically conducting doped polyacetylene film and method of preparing same |
US4269738A (en) * | 1978-11-03 | 1981-05-26 | Allied Chemical Corporation | Electrically conducting polymers |
JPS5611939A (en) * | 1979-07-10 | 1981-02-05 | Japan Synthetic Rubber Co Ltd | Production of doped acetylenic polymer |
US4394304A (en) * | 1982-01-29 | 1983-07-19 | Massachusetts Institute Of Technology | Electrically conducting polymer blends |
-
1981
- 1981-07-03 FR FR8113157A patent/FR2508914B1/fr not_active Expired
-
1982
- 1982-06-25 EP EP82401182A patent/EP0069641B1/de not_active Expired
- 1982-06-25 DE DE8282401182T patent/DE3267397D1/de not_active Expired
- 1982-07-02 JP JP57115307A patent/JPS588747A/ja active Pending
- 1982-07-06 US US06/395,294 patent/US4481132A/en not_active Expired - Fee Related
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4204216A (en) * | 1978-05-04 | 1980-05-20 | University Patents, Inc. | Electrically conducting doped polyacetylene film exhibiting n-type electrical conductivity and method of preparing same |
Also Published As
Publication number | Publication date |
---|---|
FR2508914A1 (fr) | 1983-01-07 |
EP0069641B1 (de) | 1985-11-13 |
JPS588747A (ja) | 1983-01-18 |
DE3267397D1 (en) | 1985-12-19 |
US4481132A (en) | 1984-11-06 |
FR2508914B1 (fr) | 1986-08-29 |
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